Oxidative transformations of betulinol

Tetrahedron

Volumn 64, Issue 39, 2008, Pages 9225-9229

  Barthel, Alexander ^a   Stark, Sebastian ^a   Csuk, René ^a  

^a MARTIN LUTHER UNIVERSITY HALLE WITTENBERG   (Germany)

Author keywords

Betulinal; Betulinic acid; Betulinol; Betulonal; Betulonic acid; Oxidation

Indexed keywords

BETULIC ACID; BETULIN; BETULONAL; BETULONIC ACID; BETUTINAL;

ARTICLE; CRYSTALLIZATION; DRUG ISOLATION; DRUG OXIDATION; DRUG PURIFICATION; DRUG STRUCTURE; LOW TEMPERATURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; ROOM TEMPERATURE;

EID: 49149128528     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.07.042     Document Type: Article

References (58)

1. Persona M., Geca T., Persona A., Richtr V., and Kraitr M. Pol. J. Chem. 82 (2008) 241
2. Nitz, T. J.; Montalbetti, C.; Mears, R.; Gai, X.; Glen, E. PCT Int. Appl. WO2008057420, 2008;
3. Chem. Abstr. (2008) 585712
4. Rajendran P., Jaggi M., Singh M.K., Mukherjee R., and Burman A.C. Invest. New Drugs 26 (2008) 25
5. Quian K., Nakagawa-Gote K., Yu D., Morris-Natschke S.L., Nitz T.J., Kilgore N., Allaway G.P., and Lee K.-H. Bioorg. Med. Chem. Lett. 17 (2007) 6553
6. Huang L., Yu D., Ho P., Lee K.-H., and Chen C.-H. Lett. Drug Design Discov. 4 (2007) 471
7. Mukherjee R., Kumar V., Srivastava S.K., Agarwal S.K., and Burman A.C. Anti-cancer Agents Med. Chem. 6 (2006) 271
8. Bi Y., Xu J., and Wu X. Zhongguo Xinyao Zazhi 14 (2005) 23
9. Tolstikova T.G., Sorokina I.V., Tolstikov G.A., Tolstiko A.G., and Flekhter O.B. Russ. J. Bioorg. Chem. 32 (2006) 37
10. Aiken C., and Chen C.H. Trends Mol. Med. 11 (2005) 31
11. Yogeeswari P., and Sriram D. Curr. Med. Chem. 12 (2005) 657
12. Ender, C.; Sauter, M. DE 10204278 C1, 2003;
13. Chem. Abstr. (2003) 607453
14. Galgon T., Höke D., and Dräger B. Phytochem. Anal. 10 (1999) 187
15. Ramadoss, S.; Siddiqui, M. J. M. PCT WO 2001064709, 2001;
16. Chem. Abstr. (2001) 661451
17. Dräger, B.; Neubert, R.; Galgon, T.; Wohlrab, W. Ger Offen DE 19713768, 1998;
18. Chem. Abstr. (1998) 689287
19. Dzhemilev, U. M.; Tolstikov, G. A.; Pokrovskii, A. G.; Salakhutindov, N. F.; Tolstikova, T. G.; Shul'ts, E. E. RU 2317996, 2008;
20. Chem. Abstr. (2008) 269455
21. Pichette A., Liu H., Roy C., Tanguay S., Simard F., and Lavoie S. Synth. Commun. 34 (2004) 3925
22. Baltina L.A., Flekhter O.B., Nigmatullina L.R., Boreko, Pavlova N.I., Nikolaeva S.N., Savinova O.V., and Tolstikov G.A. Bioorg. Med. Chem. Lett. 13 (2003) 3549
23. Kim D.S.H.L., Chen Z., Van Tuyen N., Pezzuto J.M., Qui S., and Lu Z.-Z. Synth. Commun. 27 (1997) 1607
24. Levandskij, V. A.; Polezhaeva, N. I.; Kuztnetsov, B. N. RU 2269541, 2006;
25. Chem. Abstr. (2006) 126094
26. Ashavina O.Y., Flekhter O.B., Galin F.Z., Kabal'nova N.N., Baltina L.A., and Tolstikov G.A. Chem. Nat. Compd. 39 (2003) 207
27. Kogai, T. I.; Kuznetsov, B. N. RU 2271364, 2006;
28. Chem. Abstr. (2006) 218258
29. Menard, H.; Cirtiu, C. M.; Lalancette, J. -M.; Ruest, L.; Kaljaca, Z. PCT 2063464A1, 2006;
30. Chem. Abstr. (2006) 604456
31. Csuk R., Schmuck K., and Schäfer R. Tetrahedron Lett. 47 (2006) 8769
32. Zhao M., Li J., Mano E., Song Z., Tschaen D.M., Grabowski E.J.J., and Reider P.J. J. Org. Chem. 64 (1999) 2564
33. Merbough N., Bobbitt J.M., and Bruckner C. J. Carbohydr. Chem. 21 (2002) 65
34. Rodriguez A., Nomen A., Spur B.W., and Godfroid J.J. Tetrahedron Lett. 40 (1999) 5161
35. Bansal R.V., Dean B., Hakomori S.-i., and Toyokuni T. J. Chem. Soc., Chem. Commun. (1991) 796
36. Jin J.-T., Tian R.-F., Liu L.-B., Zhao Y., and Li T.S. Synth. Commun. 36 (2006) 1823
37. Um S.J., Park M.S., Park S.-H., Han H.-S., Kwon Y.-J., and Sin H.-S. Bioorg. Med. Chem. 11 (2003) 5345
38. Saphier S., Hu Y., Sinha S.C., Houk K.N., and Keinan E. J. Am. Chem. Soc. 127 (2005) 132
39. Menger F.M., and Lee C. Tetrahedron Lett. 22 (1981) 1655
40. Bowden K., Heilbron I.M., Jones E.R.H., and Weedon B.C. J. Chem. Soc. (1946) 39
41. Westheimer F.H., and Nicolaides N. J. Am. Chem. Soc. 71 (1949) 25
42. Roshchin, V. I.; Shabanova, N. Yu.; Vedernikov, D. N. RU 2190622, 2002;
43. Chem. Abstr. 139 (2003) 69394
44. Pezzuto, J. M.; Kim, D. S. H. L. U.S. Patent 5,804,575, 1998;
45. Chem. Abstr. 129 (1998) 230869
46. Mazzitschek R., Mülbaier M., and Giannis A. Angew. Chem., Int. Ed. 41 (2002) 4059
47. Bal B.S., Childers Jr. W.E., and Pinnick H.W. Tetrahedron 37 (1981) 2091
48. Robertson A., Soliman G., and Owen E.C. J. Chem. Soc. (1939) 1267
49. Tiwar K.P., and Choudhary R.N. Pol. J. Chem. 53 (1979) 551
50. Sundararamaiah T., Ramraj S.K., Rao K.L., and Vimalabai V. J. Indian Chem. Soc. 53 (1976) 638
51. Ziegler H.C., Franzyk H., Sairafianpour M., Tabataba M., Tehrani M.D., Bagherzadeh K., Hagerstrand H., Staerk D., and Jaroszewski J.W. Bioorg. Med. Chem. 12 (2004) 119
52. Monaco P., and Previtera L. J. Nat. Prod. 47 (1984) 673
53. Bhattacharyya J., Kokpol U., and Miles D.H. Phytochemistry 15 (1976) 431
54. Ruzicka L., and Rey E. Helv. Chim. Acta 24 (1941) 529
55. Choi S.Z., Yang M.C., Choi U.S., and Lee K.R. Arch. Pharm. Res. 29 (2006) 203
56. Ito J., Chang F.R., Wang H.-K., Park Y.K., Ikegaki M., Kilgore N., and Lee K.H. J. Nat. Prod. 64 (2001) 1278
57. Flekhter O.B., Ashavina O., YuBoreko E.I., Karachurina L.T., Pavlova N.I., Kabal'nova N.N., Savinova O.V., Galin F.Z., Nikolaeva S.N., Zarudii F.S., Baltina L.A., and Tolstikov G.A. Pharm. Chem. J. 36 (2002) 303
58. Sun I.C., Wang K.H., Kashiwada Y., Shen J.K., Cosentino L.M., Chen C.H., Yang L.M., and Lee K.H. J. Med. Chem. 41 (1998) 4648